You may need a newer version for ctr-httpwn to work. Anyway, 9.4.0 is not a good version to be on, as it doesn't support seed keys (those were introduced in 9.5) so newer eShop games won't work at all and you have to find cryptofixed versions of them (that's not a problem for .3DS roms though)
Are you talking about your sysNAND version? If so, Gateway doesn't normally support sysNAND versions above 9.2, although if you have A9LH/B9S or you install B9S you can use it on any firmware version 11.2 or below. Don't update your sysNAND any further, only update emuNAND. http://3dsdb.com has a list of which update game carts come with, if you find one for your region with 11.2 on it and enter the Gateway menu (boot GW with the cart out or hold L when booting GW) and boot Gateway Mode while holding D-Pad Up, it disables game cart update blocking so you can update your emuNAND to 11.2 using a ROM. Only do this on emuNAND though, I can't stress that enough.

Been out of the game for a long time, just getting back into it now... have an early Gateway...I assume it's still good if I update it?

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Why even use Gateway at this point? Gateway is way too obsolete and there's no reason to use it today. Also they have essentially abandoned the development of Gateway since no one buys their flashcart anymore and they're making no profit.

Your best bet is to follow 3ds.guide, install boot9strap and Luma3DS (and BootNTR if you want cheats), update to Firmware 11.4, and completely ditch Gateway.